Remote Chief Operating Officer

Summary

Join TRAILS as the inaugural Chief Operating Officer to drive strategic growth and transformation as the organization scales its impact. Reporting directly to the CEO, you will oversee operations, finance, and people functions, working closely with senior leadership and the Board of Directors to align these areas with the organization's mission.

Requirements

• 10+ years of relevant experience, including a minimum of 5 years in a senior executive leadership role overseeing finance, operations, and/or people functions (ideally all three)
• Exceptional strategist: Proven ability to transform vision and big goals into clear priorities, strategies, and actionable plans, especially in ambiguous and uncertain contexts
• Exceptional operator: Proven experience leading business operations, with expertise in building and adapting processes to meet organizational needs and influencing decisions through clear and confident communication
• Human-centered leadership: Consistently models organizational core values and ensures DEI and human-centered principles are deeply embedded in all aspects of operations, finance, and people policies, fostering an inclusive and equitable workplace
• Strong team leader and manager: Proven success in building, managing, and leading a high-performing, multi-layered team, including senior staff capable of leading their functions autonomously and with excellence
• Functional expert with broad range: Strong working knowledge and interest across finance, people, and operations, with demonstrated expertise in at least one of these areas, particularly finance or people operations
• Business acumen: Demonstrated experience in setting strategic goals, managing budgets, and tracking organizational performance. Expertise in financial planning and budgeting, with experience managing mixed revenue streams (philanthropic, legislative, public)
• Autonomy and collaboration: Ability to work independently while knowing when to seek collaboration with the CEO and other key stakeholders

Responsibilities

• Collaborate closely with the CEO and Board to define and execute the strategic plan, ensuring it aligns with TRAILS' vision and mission
• Transform strategic goals into actionable strategies, leading key initiatives that secure the organization's sustainability and extend its reach and effectiveness
• Provide essential financial insights to inform organizational decision-making regarding program development, partnership and expansion strategies, fundraising, and policy activities to ensure a strategic and comprehensive approach to growth and impact
• Cultivate and contribute to a culture of innovation and continuous improvement, generating and encouraging new ideas, technologies, and methodologies to enhance TRAILS' operational excellence, effectiveness, and pathways to success
• Employ adept change-management skills to lead the organization through transitions and growth phases, effectively managing resistance and building team engagement and buy-in
• Spearhead clear, transparent, and consistent internal communication, ensuring all staff members are informed, aligned, and motivated towards shared goals
• Manage reporting teams across key organizational verticals – Finance, Operations and People – including responsiveness to exceptional performance and effective management of staff needing additional support
• Provide mentorship and development opportunities to build a strong, high-performing team capable of leading their respective areas with autonomy and excellence
• Assess and ensure TRAILS' financial systems are designed and built to support multi-state program expansion, rapid organizational growth, and long-term sustainability despite complex and unpredictable revenue streams
• Develop and implement a sustainable economic model that optimizes a mix of diverse funding sources including public, private, and contract revenue
• Implement detailed financial planning and reporting systems, proactively identifying immediate and long-term fiscal risks, enhancing the organization's ability to make data-driven decisions and transparently share progress with stakeholders
• Identify, evaluate, and recommend potential partnerships that provide financial or operational benefits to the organization
• Align the work of the finance vertical and the external affairs team across diverse funding sources, including public, private, and contract, ensuring compliance and optimization of funds
• Manage and coach direct reporting teams to successfully build and adapt systems to optimize cross-functional coordination
• Partner with development colleagues to identify fiscal gaps and risks, establish fundraising goals, and design and execute strategic revenue plans
• Collaborate with policy colleagues to set legislative funding goals and outline public revenue strategies, pursuing and integrating state, federal, local, settlement, departmental, and grant funding
• Assess existing operational systems, tools, and supporting teams, identifying infrastructural strengths as well as gaps, risks, and areas for improvement
• Swiftly lead toward organizational sustainability by designing, developing, and implementing needed changes to enhance efficiencies in TRAILS' virtual work environment
• Oversee the development and management of IT infrastructure, data management practices, and physical assets, ensuring they meet the needs of staff and program delivery
• Ensure streamlined and standardized operational processes and systems across departments, promoting efficiency, effectiveness, and alignment with the organization's strategic goals
• Partner with the Operations team in the design and establishment of all systems to support contract management, legal compliance, document review and execution processes, and deliverable oversight, navigating disputes, terminations, and liability issues to safeguard organizational interests
• Conduct a thorough appraisal of TRAILS' people systems, processes, and structures and oversee completion of priority deliverables as needed to evolve and stabilize the organization
• Oversee the People Team leadership in developing and maintaining a comprehensive talent management framework that integrates competency-based hiring, performance evaluation, and staff growth and retention
• Support the building and enhancement of established HR functions, including payroll, benefits, and wellness programs
• Champion diversity, equity, and inclusion initiatives throughout the organization, ensuring that DEI principles are deeply integrated into all aspects of operations, culture, and strategic planning to foster an inclusive and equitable workplace

Benefits

• Comprehensive benefits package including medical, dental, and vision as well as a 403B with a safe harbor match and short and long term disability
• Generous holiday and paid time off package